


The Emerald Umbrella

by ArrowGirl20



Category: Arrow (TV 2012)
Genre: F/M, alternative universe
Language: English
Status: In-Progress
Published: 2016-12-04
Updated: 2017-07-03
Packaged: 2018-09-06 12:56:48
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 10
Words: 8,172
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8752441
Author URL: https://archiveofourown.org/users/ArrowGirl20/pseuds/ArrowGirl20
Summary: All it took was a little rain and a emerald umbrella for Oliver and Felicity to take their relationship to the next level. CURRENTLY BEING EDITED AND REVISED.





	1. Present

**Author's Note:**

> This story started out as a one shot, but a lot of people expressed interest in reading more. So, I have a plan for this story and will start posting more chapters soon.

Present 

Felicity’s phone beeped,  as she was throwing away her trash at Big Belly Burger. Sighing, Felicity fished her phone out of her pocket and opened the text.

_"Where are you? The she devil is looking for you and she looks angry."_

A loud groan escaped from Felicity. Of course, Isabel was looking for her, she always was. Ever since Felicity took over at Queen Consolidated, QC’S VP was always looking for new ways to ruin her life. But it wasn’t Felicity’s fault that Robert Queen named Felicity acting CEO and all Isabel got was second rank. Felicity guessed that being the mistress of the former QC CEO didn’t give her the automatic CEO position.

Felicity sent a quick text back to her executive assistant, Sara Lance, before rushing out onto the sidewalk.

The sudden shock of cold rain brought Felicity out of her dreadful thoughts of the conversation she and Isabel were going to have once she got back to the office.

“Shoot!” Felicity shouted. She forgot to bring her coat with a hood and now she was going to look like a drowned rat. That’s a great look for the new CEO of Queen Consolidated. She tried to cover her head with her purse, but that wasn’t helping at all. So, she hunched down and dashed in the direction of her car. Felicity was so focused on her task, that she didn’t see the man that lifted an emerald umbrella over her head.

“It looks like you could use some help.” A deep voice came from her right.

“Yes, I could, thank…” Felicity’s voice died in her throat as she looked up at the familiar man who came to her rescue.

“Mayor Handsome.” Felicity smirked as she looked up into the face of the man with crystal blue eyes and the stubble covered jaw. The face of the Mayor of Star City.

‘Felicity, I told you not to call me that.” Oliver groaned as he took her hand in his.

“I know, but it is so fun seeing you get all huffy at the media calling you that, I couldn’t resist."

Oliver rolled his eyes at her.

“So, what are you doing here? Not that I am not glad to see you, you saved me from looking like a mess in front of Isabel, but aren’t you suppose to be at City Hall right now?.” Felicity babbled out.

“I was just on my way to City Hall when I saw you step out of Big Belly Burger, and thought I would offer some assistance.”

Felicity nodded and squeezed his hand in a thank you gesture.

Oliver had been Felicity’s best friend since she moved to Star City five years ago to work at QC. The first time Oliver stepped into Felicity’s cubicle, they could both feel the instant connection.

Now five years later, Felicity is ready to take the next step, but Oliver seems clueless. Maybe it is time to take matters into her own hands.

Felicity took the umbrella from Oliver’s hand. He gave her a questioning look, but Felicity just smiled and took that final step into his personal space.

“Oliver will you go out to dinner with me?” Their faces were so close their noses were almost touching.

Standing so close to Oliver, Felicity could hear his breath speed up and see his eyes widen.

She was starting to shuffle her feet in nervousness because his silence was lasting longer than she would have liked.

Oliver suddenly placed his hand around on hers on the umbrella and leaned in for a soft kiss on her lips.  
Once he pulled away, Oliver whispered,

“I thought you’d never ask.”

Felicity leaned back in surprise. “What?”

Oliver wrapped his arms around Felicity and gave her a sweet kiss on her cheek.

“Yeah, I have not been blind to your feelings for me and I have known for a while that you wanted to take the next step. I just wanted to make sure I was ready and I am, so yes I would love to go to dinner with you.”

Felicity gave Oliver a huge grin and pushed up on her toes for a sweet, but longer kiss. When they broke apart, both their phones beeped with incoming texts.

Sighing, Felicity stepped away with Oliver’s umbrella still in hand. She called out to him,

“I’ll call you with details about our date, but go be Mayor Handsome.”

Oliver huffed out a laugh and called back,

“Alright, if you go be CEO.”

Felicity nodded and twirled the umbrella in her hand and smiled thinking that their romantic relationship all started with Oliver’s emerald umbrella.


	2. Five Years Ago

**Summary for the Chapter:**

> Felicity meets a certain CEO's son.

**Notes for the Chapter:**

> Just like I mentioned in the first chapter, this was originally a one shot. Several people expressed interest in reading more, so I am writing more chapters. The last chapter is set in present time while this is set 5 years before. I will try to keep a Monday posting schedule, we'll just see how it goes. Anyways, enjoy! 
> 
> As always, all mistakes are mine!

Five Years Ago

Felicity set her box of personal belongings on her desk. She took a moment to take in her very small and not very private cubicle.

_Well, Smoak, this is it. Your new home for the forseeable future. Hopefully I won't be stuck in here forever._

Nerves were flaring up in the pit of her stomach and the exhaustion from moving to Star City from Boston all in one week, was finally catching up to her. 

After downing two cups of coffee to keep her awake, Felicity’s hands were shaking as she put her belongings in their places.

Sitting down on her rolling chair, she tried to take huge breaths to calm her down. This didn’t help, so she put head between her knees.

“Ms. Smoak?” A strong male voice called out from down the hallway. She could hear several footsteps coming in her direction. She quickly pulled herself together and jumped up from her rolling chair.

“Ye…yes?” She stuttered out as she came face to face with the one and the only, Robert Queen.

“Ms. Smoak, right?” He held out his hand for her to shake.

Felicity put her hand in his praying that the CEO wouldn’t see her hands shaking.

“Correct. That’s me. It says so on my nameplate on my desk and obviously I wouldn’t answer to it if it wasn’t my name.” Felicity babbled out in a nervous rush.

Suddenly, laughing broke out on Mr. Queen’s right side. She looked over to see the hottest man she ever laid eyes on. Clear blue eyes met hers in amusement. He was tall and muscular with light brown hair. He had stubble covering his jaw like he hadn’t shaved in a few days. He was simply beautiful.

Mr. Queen sighed in irritation, “Anyway, Ms. Smoak, I wanted to come down here and personally introduce myself to the brightest new mind to join our team.”

“It is a pleasure to meet you and I am really grateful to you for hiring me on. I hope I can make you proud.” Felicity returned in excitement.

“I am sure you will, unlike my son over here.” Mr. Queen’s voice turned cold on the last few words.

Felicity turned to look at Mr. Queen’s son just as the amusement on his son’s face turned to hurt then to anger and finally settled on a blank expression.

Felicity blinked her eyes a few times in amazement. She couldn’t believe that he would say that about his own son with his son and her standing right there.

“Well, I am sure he has done tons of things to make you proud.” Felicity turned a warm smile to his son.

She saw a flicker of warm reach the son’s eyes under his blank expression.

Felicity reached out her hand to him and introduced herself,

“Hi, I’m Felicity Smoak.”

His son took her hand in his warm, but rough grasp. There was a shock of electricity that shot through both their arms causing both of them to let out a gentle gasp.

He recovered quicker than she did and replied with, “Oliver Queen, the CEO’s disappointing son.”

She hated that he thought of himself like that and hated his father more for telling him that in the first place.

Pushing her anger down, Felicity pasted on a fake smile.

“Well, if you don’t mind Mr. Queen, Oliver, I have some work I have to get back to.” Felicity sat back down in her rolling chair.

“Of course, Ms. Smoak. Oliver you should learn from Ms. Smoak’s work ethic. You might just be running the company one day if you did.”

Oliver rolled his eyes behind his father’s back.

“With thinking like that, I could one day become mayor of Star City.” Oliver whispered sarcastically, as he watched his father walk away.

“Hey, you never know. You could be mayor of Star City one day.” Felicity stated, turning to her computer and starting it up.

Felicity felt Oliver’s eyes on her face before he leaned his arms against the divider on her cubicle.

“You really think so? Me? A guy who dropped out four Ivy League colleges, I don’t think so. I would be lucky to even get a job here working under my father.” Oliver’s eyebrow lifted in skepticism.

“Of course you can. I grew up in Vegas with my mother. We didn’t have very much money, but I worked my butt off to get a full ride scholarship to MIT. If I can do that, than you can definitely do anything you put your mind to. Don’t let your father put you down like that.” Felicity turned to stare into Oliver’s blue eyes.

They stayed like that for a few minutes before Oliver broke the connection. He tapped his hands on the side of the divider.

“Thank you for the advice. I would love to stick around and chat some more, but my father is probably wondering why I am not listening to his boring lectures.”

Felicity nodded her head, “Okay, I’ll see you around.”

Oliver nodded back and started for the elevator, but stopped and turned around to ask,

“Hey, could we go out for coffee sometime? I could use some more of your awesome advice.”

Felicity smiled, “Yeah, I would like that. Just come down and get me when you want to go.”

Oliver’s grin spread across his whole face and it even reached his eyes.

“Sure.”

He turned and disappeared into the elevator.

Felicity thought that living in Star City wouldn’t be so bad after all.

**Notes for the Chapter:**

> What do you think?


	3. Present

**Summary for the Chapter:**

> Felicity deals with Isabel.

**Notes for the Chapter:**

> We are back to present time for Felicity and Oliver. There will be a flashback every other chapter. You will learn how they got to the point in their relationship that they are currently at in the present time. I hope that makes sense.
> 
> For ex: This chapter is present time, the next chapter will be four years ago.
> 
> Enjoy!
> 
> As always, all mistakes are mine.

 

Present

Felicity stepped off the elevator on the top floor of QC. She was twirling the handle of Oliver’s emerald umbrella in her hand.  Still reeling from the fact that she and Oliver had a date, she didn’t see Sara coming straight for her.

“Felicity! Thank God, you’re here. The she devil is in your office and she is angry. She spent the last twenty minutes glaring at me, so you owe me.” Sara gave Felicity a couple of files for her to look over.

“I’ll get your favorite coffee for you tomorrow.” Felicity gave Sara a sheepish look.

“Okay, you’re forgiven. Now, please, go deal with her.”

Felicity turned to her glass office door.

In her office, she could see Isabel in one of the chairs in front of her desk. Her cold demeanor could be seen from where Felicity stood. She shivered then steeled her back.

_You can handle Isabel, Felicity. Show her whose boss._

Felicity opened her office door and walked to her desk. Sitting in her office chair, Felicity finally acknowledgement Isabel with,

“It’s always a pleasure to see you, Isabel.” Felicity painted a fake smile on.

“No, it’s not. I don’t like you and you don’t like me, so let’s just get down to business.”  Isabel’s face stayed impassive the whole time she spoke.

“Alright, what’s business would you like to discuss?” Felicity really had to work on her stoic face because Isabel has it down packed.

Isabel crossed her legs and responded with, “The Company is over budget. To cut spending, I suggest we cut a couple thousand jobs.”

Felicity quirked an eyebrow, “I wasn’t aware we were over budget.” Felicity retrieved one of the files that Sara gave her. She quickly glanced over the data and saw nothing of concern. “It looks like we’re just _under_ budget. I don’t see the need to cut any more jobs.”

Isabel folded her hands on her lap. This was the only sign Felicity saw that was woman was irritated.

“We are toeing a fine line, Ms. Smoak. The more under budget the company looks the better. So, I suggest we cut those jobs.”

Felicity narrowed her eyes, “Ms. Rochev, I don’t see a need to cut jobs. Like you said yourself, we’re just towing the line. And by not cutting jobs, we already look good to the outside business world, right?”

Isabel’s eyes turned murderous, “What do you know about the outside business world? You don’t belong in the CEO’s chair; you still belong in the broken rolling chair downstairs in the IT department.”

“Well, that was not what Mr. Queen thought, now was it?” Felicity stated leaning back in her CEO chair.

Isabel smacked Felicity’s desk with the palm of her hand.

“Robert should have never picked you! I will never understand why?”

“Maybe he thought I had the company’s best interest at heart. Maybe he didn’t want another power hungry, cold person to be the face of his company. Or maybe it’s the fact that, he didn’t want to ruin his company’s reputation by putting the woman’s he was sleeping with in charge.” Felicity smirked, satisfied at Isabel’s shocked face.

“This isn’t over!” She growled while exiting Felicity’s office.

“I think it is!” Felicity called back to Isabel’s retreating form.

Sara gave Felicity a thumb’s up for telling the she devil off and Felicity smiled back.

After that exchange, Felicity got to work on her mountain of paperwork that had to be looked over and signed by the end of the night.

She was startled out of her task by the sound of her phone ringing. Looking at the caller ID, Felicity broke out into a huge grin.

“Hey, Mayor Handsome.”

“Felicity…” Oliver growled out.

“Sorry. What’s up? How are things at City Hall?”

“Not bad. Just a lot of meetings and signing documents, nothing I can’t handle.”

“Good, so, I could really use one of our coffee sessions right now.” Felicity sighed out a wary breath.

“Why? What happened?” Oliver’s concern warmed her heart.

 “I told you I had to deal with the she devil this afternoon and she was a little more difficult than usual.” Felicity told Oliver.

“You put her in her place, didn’t you?” Oliver teased.

“Well, of course. I always win against her.” Felicity stated.

“What is the score now? Like a million to zero?”

Felicity huffed out a laugh, “More like a billion to zero.”

“Sorry, my apologies.” Oliver teased. “So, how about Friday night?”

“For what?” Felicity questioned.

“Our date. I’ll meet you downtown at the one Italian restaurant that you liked so much. Say around eight?” Oliver asked.

Felicity took a deep breath before she answered. She couldn’t believe this was actually happening.

“Hey, I thought I was supposed to call you about the details of our date? But yeah, eight sounds cool.” Felicity teased. She didn’t mind him picking out the place of their date. She only said she would, to get his butt into gear.

“I know, but since you asked me, I thought it was only fair that I would make the plans.”

“Okay.” Felicity agreed.

“Alright, talk to you soon?” Oliver’s gentle voice never failed to make Felicity melt.

“Yeah.” Felicity replied.

“Goodnight.” Oliver spoke.

“Goodnight.”

Once Felicity ended the phone call, she finished saving her work and shutting down her computer.

All she had to do now was find a dress for her date with Oliver and she only had a few days to do it in.

That might be a challenge, but she knows someone who could help.

**Notes for the Chapter:**

> What did you think?


	4. Four Years Ago

**Summary for the Chapter:**

> Felicity meets Oliver for one of their coffee sessions.

**Notes for the Chapter:**

> This is set four years before present time and a year later from the Five Years Ago chapter. You'll learn a little more about Felicity and Oliver's friendship. Enjoy!
> 
> As always, all mistakes are mine.

Four Years Ago

Felicity rushed to the front door of the local coffee shop that Oliver and she meet at every Saturday. She opened the door and the smell of hot coffee and baked goods assaulted her nose. She looked around until she caught sight of Oliver at their usual table. Smiling she walked over to him, wrapping her arms around his neck.

“Sorry, I’m late. Mr. Steele had me working on a code until late last night.” She turned to kiss his stubble covered cheek before stepping back so Oliver could get up. He stood up and turned around. He had a smile on his face while he wrapped his huge arms around her. He leaned down to kiss her cheek. Every time he did that, she got butterflies in her stomach.

“It’s fine. I just got here myself. Up late studying, you know.” Oliver said while taking his seat again.

“What? No late night clubbing with Tommy. I’m shocked.” Felicity gasped in fake horror. She giggled when she saw the glare on his face.

“Ha, ha. Thank you, Ms. Sarcasm. You know your night was no less boring than mine.” Oliver smirked when she gave him a pointed look back.

“True, okay, enough joking around. Tell me how the studying is really going?” Felicity asked as she picked up her coffee that Oliver already ordered for her. 

“It is going okay. Since I started at Star City University, I feel like everyone is waiting for me to fail.” Oliver sighed and rubbed his face with his hand.

“You are not going to fail. You’ll have your political science degree in no time. And you know, if you need help, I am always here.” Felicity placed a reassuring hand on Oliver’s where he had it wrapped around his coffee mug.

“Thanks, Felicity.” He ran a thumb over the hand that was on his. “But enough about me, what was the project Walter had you working on.”

It was Felicity’s turn to sigh. She ran a hand over her messy pony tail before wrapping both her hands around her mug again.

“Well, as you know, QC is merging with Stellmoor International and their VP, Isabel Rochev, is working to get the company’s programs all in working order by the time the merger is complete. It has us all working overtime. That woman is the she devil.”

“I think my mother would agree with you.” Oliver sipped his coffee.

“That would be the first time Moira and I have ever agreed.” Felicity replied shocked. She thought the two women would actually like each other. Felicity raised her eyebrows in a question waiting for the rest of the story.

“Isabel came over for dinner Thursday and was all over my father. I could literally see the smoke coming out of my mother’s ears. I don’t think that is going to end well.” Oliver stared off into space probably remembering that night.

“Do you think your father would cheat on your mother?” Felicity questioned in concern.

“I don’t know. He has always had a wondering eye, but I don’t think he would cheat on my mother with her. I guess only time will tell.”

“What are you doing tonight?” Felicity asked, changing the subject. She could see the discomfort written all over Oliver's face.

“Tommy actually wanted to go clubbing tonight, so I figured I would just go get a drink with him.” Oliver took the last sip of his coffee before standing up.

Felicity stood up too, “Don’t have too much fun. And call me when you get home, okay?”

She wrapped her arms around him again.

He returned her hug, “Okay, mom.”

Felicity slapped his back, “Shut up.”

“Call you later?” Oliver asked.

Felicity nodded, “I'll be waiting.”

Oliver kissed her forehead before letting her go. He smiled at her before he walked out the door.

She smiled back and watched him go. She didn’t know when she started have feelings for him, but she knew they were only growing stronger.

Only problem was, she didn’t know if Oliver felt the same.

**Notes for the Chapter:**

> Thoughts?


	5. Present

**Summary for the Chapter:**

> Felicity looks for a dress and gets some help from a friend.

**Notes for the Chapter:**

> There will be one more chapter from Felicity's POV before switching to Oliver's. Enjoy!
> 
>  
> 
> As always, all mistakes are mine.

Present

The rain pelted down on the emerald umbrella that Felicity held in her hand. Rain was in the forecast for all week, but Felicity didn’t mind.

Every time she gazed upon Oliver’s umbrella, she was reminded of when he said yes to her.

“Hey, Felicity!” A woman’s voice called from behind her.

Felicity spun on her heels to see who it was. Thea Queen was walking with her own umbrella towards her.

“Hi, Thea! What’s going on?” Felicity moved her umbrella to give Thea a kiss on the cheek.

“I was looking for you. I heard that you had a hot date with my brother. It’s about time.”

Felicity grinned.

“Yeah, I know, but waiting was worth it. It has been a hard couple of years for the both of us.”

Thea nodded in agreement,

“Yeah, all that happened with my mom and dad, then you and Ollie dating other people, it never seemed like the right time, huh?”

“No, it didn’t, but we’re ready now. So, why were you looking for me?” Felicity asked closing the emerald umbrella. She stepped under Thea’s umbrella and linked her arms with Thea.

“Well, since you have a date on Friday, I figured you’d need some help finding the perfect dress.”

Felicity turned to Thea and squeezed her arm.

“Yes! I was just going to call you to help me.”

“Well, I am always here to improve your outfits.”

“Oh, I know. We’ve had some memorable shopping trips haven’t we?”

Thea smiled, obviously remembering the time when she turned up Felicity’s wardrobe to a ten and it had Oliver taking second glances for an entire week.

“What color were you thinking? Like a fiery red or a bold black? ” Thea stopped in front of the QC building.

“Let’s go fiery red. I want Oliver’s jaw to drop off.” Felicity smirked.

“Fiery red it is. I’ll meet you on your lunch break?” Thea questioned. She let Felicity’s arm go.

“Yeah, I’ll text you.” Thea nodded and walked off.

Felicity headed up the steps to the front door of QC.

_______________________

“Do you have it on?” Thea called from the other side of the dressing room door.

“Yeah, I’ll be out in a second.” Felicity called back. She was zipping up the fiery red dress that Thea placed in her hands.

Turning towards the mirror in the dressing room, Felicity gasped. It was perfect. It had a sweetheart neckline; it hugged her body all the way down to her knees. But what made the dress perfect was the fact that it was backless.  She looked amazing and more importantly felt amazing in the dress.

“Come on, Felicity, I want to see it on you!” Thea huffed out in impatience.

“Okay, okay. I’m coming! Don’t get your panties in a twist.” Felicity threw open the door to the dressing room and came face to face with a shocked Thea.

Spinning around to give Thea the full view,

“So, what do you think? Will it cause Oliver’s jaw to fall off?”

“WOW. You won’t cause Oliver’s jaw to fall off. You’ll just cause him to pass out from how amazing you look in this dress. Just WOW, Smoak.” Thea’s mouth came up in a smirk.

“I know, right. This is the one.” Felicity smiled at Thea.

“Definitely, now, go get dressed. You have to be back at the office in 20 minutes.” Felicity nodded before heading back inside.

________________________

Before Felicity headed inside of QC, Thea grabbed her arm to gain her attention.

“Felicity?” Thea serious tone caught Felicity’s attention.

“Thank you.”

“For what?” Felicity’s eyebrows scrunched in confusion.

“For being my brother’s best friend, for giving him advice so he could believe in himself, for loving him unconditionally.” Tears welled up in Thea’s eyes in turn causing Felicity’s to well up to.

“You’re welcome; I did all those things because I love him. I’m in love with him.” Felicity explained taking Thea’s hand in hers.

Thea squeezed her hand,

“Oliver did all those things for you too. For the same reason, because he loves you and is in love with you.”

 A few tears escaped Felicity’s eyes. Thea reached up and wiped them away.

Felicity just nodded in response. She was too overwhelmed with emotion to answer right then.

“Well, I better let you go. We should hang out sometime next week. You can tell me all about your date, okay?” Thea let go of Felicity’s hand and stepped in the opposite direction of Felicity.

“Okay.” Felicity agreed. She saw Thea nodded and watched her disappear into the crowd on the sidewalk.

She is going to have one awesome sister-in-law one day. Felicity thought with a smile before turning to head back to work.

**Notes for the Chapter:**

> Thoughts?


	6. Three Years Ago

**Summary for the Chapter:**

> Felicity learns some surprising news while comforting the Queens.

**Notes for the Chapter:**

> This is the last chapter from Felicity's perspective, then we are switching over to Oliver's for awhile.
> 
> As always, all mistakes are mine.

Three Years Ago

“Robert Queen and Moira Queen have divorced after….” The news reporter’s voice drifted in the background while Felicity held Oliver’s head in her lap.

Felicity was running her hands through his hair in comfort.

“You were right, you know?”

“About what?” Oliver murmured.

“You told me that your father and Isabel working together would only end badly and you were right.”

Oliver turned his head to look up into Felicity’s eyes.

“It’s not all bad. At least the affair wasn’t made public.”

“True, I just feel sorry for your mother and sister and you.” Felicity ran a hand over Oliver’s cheek.

Oliver huffed out a sarcastic laugh,

“Don’t be Felicity. My mother is grateful for the divorce. She couldn’t handle Dad’s trysts and was glad to drop the happy marriage façade. I’m siding with my mother on this one. You saw how my father treated me and I’m glad I don’t have to deal with his verbal abuse anymore. Thea on the other hand is taking it harder. She is her Daddy’s little girl. She is still locked up in her room, not wanting to talk to anyone.”

“Maybe I could try to talk to her. Lord knows, I have had my fair share daddy issues too. Maybe we could find some common ground.”  Felicity went back to running her fingers through his hair.

“Well, you can try. I don’t know if she is ready to listen to anyone yet.” Oliver turned his head back towards the television.

They stayed like that for a few more minutes until they were pulled apart by a woman bursting through Oliver’s bedroom door. Oliver jumped up from the couch, leaving Felicity on the couch in a state of confusion.

“Oliver, I heard about your parents and rushed right over.” The woman strode up to Oliver and enveloped him in a hug.

As Felicity watched the two embrace, Felicity felt her heart drop into her stomach.

Oliver moved out of the hug to face Felicity.

 “Felicity, this is my girlfriend, McKenna Hall.”

With those words, Felicity’s heart moved from her stomach and crashed to her feet.

“Girlfriend? The last time I checked, you didn’t have a girlfriend.” Felicity tried to keep her voice calm, but it was a struggle.

Oliver rubbed his neck in embarrassment.

“We met a few weeks ago and I didn’t want to say anything to you unless it was official. Now it’s official.”

Felicity didn’t know what to do with this new information, except be civil.

Felicity took in a deep breath to steel herself. She moved from in front of Oliver’s couch to stand in front of McKenna. She held out her hand to introduce herself.

“Hi, McKenna, I’m Felicity Smoak, Oliver’s best friend.”

McKenna took her hand and gave Felicity a warm smile.

“I know who you are. Oliver talks about you all the time. It’s a pleasure to finally meet you; I just wish it was under better circumstances.”

 Felicity hummed in agreement before backing towards Oliver’s door. She stabbed her finger over her shoulder saying,

“I am going to leave you two, so you can talk. I’m going to go check on Thea.”

Oliver looked at her with confusion, but just nodded, not wanting to ask why she was suddenly leaving.

____________________

While walking to Thea’s room, Felicity tried to keep her tears in check. Her bruised heart was not the most important thing right now. Thea was.

Felicity reached Thea’s room and knocked on the door.

“Thea, can I come in? It’s Felicity.”

She heard a muffled, “Yeah”, come from somewhere inside the room.

She opened the door to see Thea huddled under her covers trying to keep in her tears.

Felicity walked over to Thea’s bed and snuggled under the covers with Thea.

“Sorry about your mom and dad.” Felicity whispered.

“It’s fine. I knew it was coming. I just didn’t want our family to break up.” Thea sniffled.

“Your family didn’t break up. You still have your mom and Oliver. And just because your father is not living with you, doesn’t mean he doesn’t love you. When my father left, he didn’t come back, so at least you still have your father.” Felicity gently wrapped her arms around the younger girl. “But, you can always come talk you me if you want. I will always be here for you.”

“That’s true. But why are you here comforting me? What about my brother?” Thea questioned.

“Your brother doesn’t need me. He has McKenna now.” Felicity voice came out sadder than she would have liked.

Thea turned her big brown eyes to Felicity’s and said,

“My brother will always need you. No temporary girlfriend will change that.”

Felicity nodded, but didn’t answer. She was in love with Thea’s brother, but he has a girlfriend now. Oliver didn’t see her that way and maybe never will. She will just have to accept that.

“Okay, enough of this depressing mood. Once you feel okay enough to go out, I am taking you shopping.” Felicity stated.

She watched as Thea’s eyes brightened and then looked over Felicity’s outfit with a disgusting look.

“Yes to shopping, but for you. You’re t-shirt and jeans combo is not working for me or you. It’s time to upgrade your wardrobe to sexy.”

Felicity rolled her eyes, but she knew she would let Thea have her way. Maybe shopping with Thea will lessen the heartache she feels over Oliver.

Maybe it was time she got over her crush on Oliver and maybe dating was in her near future.

**Notes for the Chapter:**

> Thoughts?


	7. Present

**Summary for the Chapter:**

> While on a coffee run, Oliver runs into an unexpected face.

**Notes for the Chapter:**

> Hey guys, its been awhile. I decided to change a couple of things after I got a few comments on the last chapter. I think the things I changed works better with this story, so I should be updating regularly again. Thanks for all the comments and kudos.
> 
> As always, all mistakes are mine.

Present

It was a rare day that week where the rain had stopped and the sun came out. Oliver took the opportunity to get some fresh air.

He walked to the local coffee shop around the corner from City Hall.

When he was ordering his coffee, Oliver decided to get a drink for Felicity. He wanted to see her beautiful face.

As he turned with both coffees in hand, the smile that illuminated his face, by thinking of Felicity, dimmed.

Oliver was face to face with a familiar face.

“Oliver! It is nice to see you again.” Ray Palmer held his hand out for Oliver to shake.

Oliver put on a friendly smile and raised both hands that were filled with coffee. Ray seemed to get his gesture because he lowered his hand.

“Hi, Ray. What are you doing in Star City?”

“Oh, just checking on the Palmer Tech branch. I actually just came from seeing Felicity.”

Oliver had to try harder to keep that smile on his face. He just hoped that Ray didn’t see his hands tighten around the coffee cups. Oliver knew he shouldn’t be jealous because Ray wasn’t Felicity’s boyfriend anymore, but he still remembers the night he found the two in the alley together. Ultimately, it led to a greater understanding between him and Felicity, but it still doesn’t mean that it hurts any less.

“Oh.” That was all that Oliver could respond with.

“Yeah, I guess congratulations are in order.”

Oliver lifted his eyebrows in confusion.

“Felicity said you and her have a date coming up soon. I’m happy for you and her.”

“Thank you.” Now, Oliver felt like a jerk. He shouldn’t have been jealous after all.

“I should get going. It was nice to see you again.”

“You too, Ray.” Oliver waved one hand in Ray’s direction and he waved back in return.

Oliver shook his head and walked towards QC.

____________________

Oliver got off the elevator on the top floor of QC. He walked to Sara’s desk to see if Felicity was available.

“Go on in, Oliver.” Sara looked up at him from her desk.

“Thanks, Sara.”

Sara nodded and Oliver went to Felicity’s glass office door. It was still weird to see her in his father’s office, but Oliver thought that she belonged there.

Felicity was hunched over her desk, looking at paperwork when Oliver set down the paper cup in front of her.

“Coffee break.”

Felicity smiled and looked up at him.

“Hey, you.” Felicity got up from her chair and walked her desk to stand in front of him.

She surprised him by getting on her tippy toes and giving him a kiss. He would never get used to the butterflies that filled his stomach every time she did that.

He kissed her back. What started as a kiss, turned into a full out make out session. Oliver didn’t mind and neither did Felicity.

The kiss only stopped when they had to take a breath.

“Thanks for the coffee.” Felicity turned to her desk and grabbed the coffee cup. She took a sip and relaxed.

Oliver took a sip of his own and sat in one of the chairs in front of her desk.

“So, guess who I ran into at the coffee shop?”

Felicity gave him a questioning look, wanting him to continue.

“Ray.”

Felicity smiled and then gave him a stern look.

“You were nice to him, right?”

“Of course. ” Oliver face twisted into a look of mock offense.

“Oh, don’t tell me you didn’t feel a little jealous at seeing him.” Felicity smirked.

Clearly, Felicity remembers all the fake niceties that Oliver gave Ray.

“Okay, maybe for just a moment, but it passed quickly when I realized I had no reason to be jealous anymore.”

“Good.” Felicity responded, moving forward to sit on Oliver’s lap. She gave him a quick peck on the lips.

Oliver checked his watch then. He had to get back to City Hall.

“Have to leave already?” Felicity questioned. She looked a little sad.

Putting down his coffee cup, Oliver wrapped his arms around Felicity and held her tight.

“Yeah, but I’ll talk to you later, okay?” He gave her a sweet kiss and then left her to enjoy her coffee.

 

**Notes for the Chapter:**

> Thoughts?


	8. Two Years Ago

**Summary for the Chapter:**

> While out with Tommy, Oliver experiences heartbreak.

**Notes for the Chapter:**

> Happy Easter everyone! Okay, so fair warning, this chapter starts out rough. But never fear, things do get better! 
> 
> Thanks to everyone who has left comments and kudos. They mean a lot!
> 
> As always, all mistakes are mine.

Two Years Ago

Oliver put the last framed picture of him and McKenna into a box and taped it up. It had been a week since they broke up and Oliver couldn’t have felt freer. There was always something about their relationship that weighed him down. They had to be perfect all the time, but perfect relationships never lasted. At least their relationship ended in a good place, with them both parting ways on good terms.

McKenna was headed to Central City for a detective position in their police department and Oliver was almost done with his four year bachelor’s degree in political science. He graduates in two weeks and he couldn’t be more excited. Finally something he could be proud of.

Oliver picked up the box that held McKenna things and walked down stairs to his car.  Closing the trunk to his car, Oliver pulled out his phone and opened it to text Felicity, but stopped.

Things had been strained between the two ever since Felicity found out about McKenna and him. He knew that he should have told Felicity about McKenna, but he was scared of her reaction. He could see that Felicity had feelings for him and if he was being honest with himself, he had feelings for her too.

It’s just that their friendship was important to him and he didn’t want to ruin it, but he already did.

Felicity had pulled away from him. She went out on a couple of dates and that made Oliver jealous.

He shouldn’t have because he had a girlfriend and now he doesn’t.

The sound of a text coming through pulled Oliver out of his thoughts.

**_Tommy: You want to go out tonight?_ **

**_Oliver: Sure. What time?_ **

**_Tommy: Nine good for you?_ **

**_Oliver: Yeah, see you then._ **

**_Tommy: Ok._ **

He got into his car and headed towards McKenna’s apartment.

__________________

“So, I said, not this time!” Tommy shouted into the space between the two men.

Oliver huffed out a laugh. Tommy always got himself into the most awkward situations ever.

Oliver shoved Tommy shoulder and led him across the street towards a small alleyway.

“Oh, look two lovers are getting it on in the alleyway.” Tommy tried to whisper that, but it came out like a shout.

The couple stopped making out and turned towards the two.

Oliver heart shattered into a million pieces when he saw who the woman was.

Felicity was standing next to a tall man with dark hair. Her lipstick was smeared all over her mouth and his. Her cheeks were as red as a firetruck.

“Oliver! Tommy! What are you two doing out here?” Felicity stuttered out. She purposely kept her eyes on Tommy.

“We were just heading down to the local bar.” Oliver gestured down the street. “Are you going to introduce us to your friend?’

“Oliver, Tommy, this is my boyfriend Ray Palmer. Ray these are my friends, Oliver Queen and Tommy Merlyn.”

Tommy shook Ray’s hand first and then Oliver took Ray’s into a tight grip. When Ray pulled his hand away, Oliver smiled at the way he was shaking out his fingers.

“I didn’t know you had a boyfriend, Felicity.” Oliver turned to look into Felicity’s eyes. She seemed to stand straighter when answering him.

“Like you told me about McKenna.”  Felicity raised an eyebrow at him. There was fire in her eyes.

Oliver pressed his lips into a tight line.

“That’s fair.” Oliver agreed.

An awkward silence hung in the air before Tommy finally clapped his hands together.

“Well, it was nice meeting you Ray, but we should get going.” Tommy reached over to shake Ray’s hand again. Oliver recognized Tommy’s attempt to defuse the situation and he was glad for it. It gave Oliver time to gather himself.

“Right, we don’t want to keep you two from your date. It was nice meeting you Ray.” Oliver shook Ray’s hand and then turned to look at _her._ “…Felicity.” Oliver swore he saw a look of longing in her eyes before she shifted to warp her arms around Ray’s waist.

“Tommy…Oliver, have a good night.”

“You too.” Oliver whispered. Giving one last look at Felicity, Oliver turned around and followed Tommy down the sidewalk.

The two men continued down the sidewalk when Tommy turned to Oliver.

“How are you doing? Are you two going to be okay?”

“I’m okay. And Felicity and I will be fine.”

Oliver hoped those words would ring true, but his heart was telling him something different.

______________

Two Weeks Later…

Oliver took a breath before knocking on Felicity’s apartment door. Oliver’s mind would not let him rest until he made things right with Felicity.

When the door opened, Oliver’s heart started to beat a little faster. She was wearing her glasses and her hair was up in a messy bun. She looked beautiful.

“Hi.”  Oliver whispered shyly.

“Hey. Oliver…what are you doing here?” Felicity leaned her head against her door.

“I…I wanted to talk to you about the other night with me and Tommy and you and Ray.”

Felicity held up her hand to cut him off. She stepped right into his personal space. Their mouths were only inches apart.

 “Before you ask, Ray and I have been dating for month. And, no, I didn’t tell you because we are not as close as we used to be. Need I remind you, you weren’t exactly forthcoming about your relationship with McKenna, so you don’t get to judge me about not telling you about Ray!” Her voice came out all growly. Oliver hated to admit it, but it was kind of hot.

Oliver shook that thought away and raised his hands in surrender.

“You’re right. I have no room to judge.   I should have told you about McKenna, but I didn’t want my relationship with McKenna to come between our friendship, but it did, and I want to apologize.”

Felicity stance seemed to loosen.

“Apologize about what?”

“If I ever made you feel, like I do now, I am deeply sorry. You have every right to date. I just want to be your best friend again. Just… I’m sorry Felicity. I want us to be okay, again.”

Her eyes seemed to soften a little.

“Okay.”

“Okay?” Oliver questioned.

“You’re forgiven…besides I missed my best friend too.”

Felicity stepped forward to wrap her arms around Oliver’s waist. Oliver breathed out a sigh of relief. He wrapped his arms around her and pressed his lips to her forehead.

She squeezed him tighter and right then Oliver knew everything was going to be okay.

**Notes for the Chapter:**

> Thoughts?


	9. Present

**Summary for the Chapter:**

> Oliver gets a visitor at the office and Oliver and Felicity's date day is finally here.

**Notes for the Chapter:**

> I'm Back! I have finally finished this story and I am so excited to share the rest with you. Thank so much to everyone who comments and leaves kudos. It means so much to me!
> 
> As always, all mistakes are mine!

Present

Oliver sat at his desk looking over some files that needed to be signed when a knock at his door diverted his attention.

Thea came skipping into his office and gracefully sat in a chair across from him.

“To what do I owe this pleasure?” Oliver questioned.

“I just came by to tell you that I helped your girlfriend pick out a sexy dress for your date.” Thea stated with a wicked gleam in her eye.

“First, she is not my girlfriend…yet. And second… thank you for helping her pick out her dress.” Oliver smiled appreciatively at his sister.

“You’re welcome, but she is your girlfriend. Has been for a long time and don’t you try to deny it!” Thea gave him a sharp glare.

Oliver sighed and then nodded. There was no arguing with Thea.

“I see you kept your promise to mom and me.”

Oliver sat there confused and then it hit him.

He laughed.

“I didn’t exactly keep that promise.”

“How?”

 Now, it’s Thea’s turn to look confused.

 “She asked me, I didn’t ask her.”

“Either way, you kept the promise. Mom and I are both proud of you.” Thea got up and walked towards his office door.

“Enjoy the dress.”

“Oh, I will.” Oliver whispered.

He couldn’t wait to see what dress they picked out, He couldn’t wait to go on this date, and it seemed he has been waiting a long time for this.

And it was finally here.

______________________

**Friday**

Oliver awoke to the sound of an incoming text. Rolling over, he picked up his phone and swiped it open.

**Felicity: It’s finally the day! Can’t wait for tonight, see you at eight!**

**Oliver: Me, neither. See you then.**

Oliver smiled before getting up and dressed for work.

_______________

The day at City Hall seemed to drag on and Oliver found himself, often lost in thought.

He knew tonight will change his life forever. And that thought actually made him excited.

He was ready for their relationship to move from the friends’ territory to a romantic one.

Oliver sat there imagining lazy Saturday’s curled up on the couch with Felicity when he heard his name being called.

“Mayor Queen? Mayor Queen!” His assistant was standing before him with a file in her hands.

Oliver shook his thoughts away,

“Sorry? What can I do for you?”

She raised her eyebrows in a silent question, but he ignored it.

She must catch on to his dismissal because she quickly handed him other the file.

 “This needs to be looked over and your thoughts on it needs to be submitted by the end of the day.”

Oliver nodded, “Okay.”

His assistant left and Oliver got back to work.

By the time the clock on his computer blinked to seven, Oliver was a bundle of nerves.

Changing into a nicer suit, Oliver headed down to the parking garage where he parked his car.

He knee was bouncing impatiently, as he maneuvered through the traffic crowded streets of downtown Star City.

Oliver checked his dashboard clock several times until he pulled up to the restaurant.

He quickly handed his keys to the valet and headed inside.

He looked around the tables until his eyes finally landed on Felicity.

The sight before him, made Oliver gasp.

**Notes for the Chapter:**

> There will be one more flashback, that is next chapter, before we get to their date. But for now, thoughts?


	10. One Year Ago

**Summary for the Chapter:**

> Oliver is out with his mother and sister when Felicity stops by.

**Notes for the Chapter:**

> Hi! This is the FINAL FLASHBACK chapter. The rest of the story will be in present day. The cliffhanger from last chapter will pick up next chapter! Enjoy!
> 
> As always, all mistakes are mine!

One Year Ago

“So, Oliver, how do the polls look?” His mother asked him from her place across the table. Oliver was out to his weekly lunch with this mother and sister. Ever since, his parents’ divorce, he made sure to at least spend one day a week with the Queen women. Today they were out to lunch at Big Belly Burger.

“I am up in the polls by seven percent. So, if they stay steady by this time next week, you will be sitting with the new mayor of Star City.” Oliver replied.

“That’s fantastic, honey, I am so proud of you.” Moira’s smile warmed Oliver chest with love. Ever since he told his mother he was running for mayor, she has been nothing but supportive. Telling his father was another story, he practically laughed Oliver out of his office. He doesn’t spend much time with his father anymore, and that is perfectly okay with him.

“Yeah, Ollie, it’s great. Maybe your first act as mayor can be getting those speeding tickets off my record.” Thea looked at her bother hopefully.

“Not a chance, Speedy.”

Thea frowned in disappointment.

“Aw, look who it is, it’s the Queens.” A familiar voice came from behind him. He smiled as his best friend wrapped her arms around his neck. She placed a soft kiss on his cheek which never failed to give him butterflies in the pit of his stomach. She placed her lips to his ear and whispered,

“Hey, Mr. Mayor.”

Oliver turned to face her. Their lips were inches apart. Felicity blushed and moved her head back.

“I’m not mayor yet, Felicity.”

She smacked his chest playfully and said, “Oh, shut it. You’re up seven percent in the polls. With a few days left until the election, you’ve got it in the bag.”

Oliver nodded. He watched as Felicity untangled herself from him to kiss his sister on her cheek and gave his mother a friendly wave.

“Felicity? When are you coming to the club? There is a girl’s night on Friday, come have a drink with me. Please!” Thea begged Felicity with her puppy dog eyes. Thea had opened her own club called, Verdant, a year ago. It is a very successful business and Oliver couldn’t be more proud of her.

Felicity always broke down when Thea gave her the puppy dog eyes.

“Fine! I’ll come. What time do you want me to be there?” Felicity asked.

“Around nine should be fine.”

Just then, Felicity phone pinged signaling an incoming text. While Felicity was checking her text messages, Oliver couldn’t help but smiling at Felicity’s and Thea friendship. It had developed after his father’s scandal. Felicity literally dragged Thea out of the mansion for shopping and they have been close ever since.

“Sorry, Queen Family, I have to get back to the office. I guess Mr. Queen and Mr. Steele have something they want to talk to me about. I’ll call you later Oliver. “

“Bye Thea, see you Friday.”

“It was nice to see you again Mrs. Queen.” Felicity rambled off her goodbyes while trying to stuff her phone back into her coat pocket.

They replied with their goodbyes and she was off out the door. His mother stared after her for a second and then turned back to Oliver, saying,

“Sweetheart, when are you going to ask that woman out on a date?”

Oliver was shocked.

“What?”

“Yeah, Ollie , when are you going to take her out? You’re not getting any younger.” Thea smirked when Oliver glared at her.

“Thea, I get asking that question, but Mom, I thought you didn’t like Felicity?”

Moira scoffed, “I have never said I didn’t like her.  I may have not been too keen on her in the beginning, but as I watched your friendship bloom. I had a change of heart. She is good for you and you are good for her.”

Oliver stilled couldn’t believe his ears, but he quickly recovered.

“I would like to, but Felicity is swamped with work and I take office in less than a week. Now is not the time to start a romantic relationship.”

“Just promise us when you’re ready, you’ll ask her out.” Thea turned the full force of her puppy eyes on him. Even his mother gave him a pointed look.

“Alright, I promise.” Oliver raised his hands in surrender.

They both nodded satisfied.

“Enough about me, what about you and Roy?” Oliver quickly changed the subject off him and looked to Thea. Thea glared at him.

“Who’s Roy?” Their mother asked.

For the next ten minutes, Thea tried to stop all questions involving Roy.

Oliver sat back and thought about the day he would finally ask Felicity out.

**Notes for the Chapter:**

> Thoughts?

**Author's Note:**

> What did you think?


End file.
